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Orsillo was born in Melrose, Massachusetts, where he often dreamed of being a broadcaster for the Red Sox. He moved to and grew up in Madison, New Hampshire, and was educated at John H. Fuller Elementary School. At the age of 12 he attended Kennett Junior High School in nearby Conway, New Hampshire. Don's family moved west just before high school. He is a 1987 graduate of Miraleste High School in Rancho Palos Verdes, California, where he played on the Marauder basketball and baseball teams.

He was NESN's play-by-play man since the beginning of the 2001 season (his first game included a no-hitter thrown by then Red Sox pitcher Hideo Nomo against the Baltimore Orioles). He also called Cal Ripken Jr.'s final game, as well as the no-hitters thrown by Derek Lowe in 2002 and young Sox pitchers Clay Buchholz and Jon Lester in 2007 and 2008, respectively. Originally, he only called the team's games which aired on NESN, with longtime Red Sox announcer Sean McDonough taking Orsillo's place alongside Jerry Remy for games which aired on local stations WFXT (2001 and 2002) and WSBK-TV (2003 and 2004). For the 2005 season, Orsillo did games on both NESN and WSBK, working with Remy.

Starting in 2006, NESN took over all Red Sox local telecasts, and until 2015, Orsillo worked with color commentator and former Red Sox second baseman Jerry Remy. In 2009, Remy was out due to health problems, and Orsillo worked with various color commentators, including Dennis Eckersley, Nick Cafardo, Sean Casey, Dave Roberts and Frank Viola. He was sometimes referred to by fans as "announcer boy," after he was given that nickname by Red Sox pitcher Tim Wakefield in a NESN commercial.[3]

On August 25, 2015, NESN controversially[4][5][6] announced that Orsillo would no longer call Red Sox games following the 2015 season, and would be replaced in 2016 by Dave O'Brien, who had called games for the Red Sox Radio Network since 2007.[7][8]

Orsillo joined the San Diego Padres for 2016, to be the successor of Dick Enberg upon his retirement after that season.[9] During the 2016 season, Orsillo worked select Padres games for television and radio broadcasts.[10]

In 2018, Orsillo called national broadcast games for Fox between the Los Angeles Dodgers and Colorado Rockies and the New York Yankees and Boston Red Sox, as well as the season finale game on September 30 between the Yankees and Red Sox on TBS. He also returned to calling the MLB Division Series games on TBS in 2018 due to Ernie Johnson unable to work the games following a diagnosis of blood clots in both of Johnson's legs.[11]